US9868250B2 - Process for the adhesive bonding of plastics pipes by means of (meth)acrylate adhesive - Google Patents

Process for the adhesive bonding of plastics pipes by means of (meth)acrylate adhesive Download PDF

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Publication number
US9868250B2
US9868250B2 US14/299,325 US201414299325A US9868250B2 US 9868250 B2 US9868250 B2 US 9868250B2 US 201414299325 A US201414299325 A US 201414299325A US 9868250 B2 US9868250 B2 US 9868250B2
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United States
Prior art keywords
component
pipe
adhesive
acrylate
meth
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US14/299,325
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US20140284924A1 (en
Inventor
Bernd Beuer
Bernhard Schoettmer
Brendan Kneafsey
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Henkel AG and Co KGaA
Henkel IP and Holding GmbH
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Henkel AG and Co KGaA
Henkel IP and Holding GmbH
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Assigned to HENKEL AG & CO. KGAA reassignment HENKEL AG & CO. KGAA ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BEUER, BERND, SCHOETTMER, BERNHARD
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Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C65/00Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor
    • B29C65/48Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding
    • B29C65/4805Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding characterised by the type of adhesives
    • B29C65/483Reactive adhesives, e.g. chemically curing adhesives
    • B29C65/485Multi-component adhesives, i.e. chemically curing as a result of the mixing of said multi-components
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C66/00General aspects of processes or apparatus for joining preformed parts
    • B29C66/50General aspects of joining tubular articles; General aspects of joining long products, i.e. bars or profiled elements; General aspects of joining single elements to tubular articles, hollow articles or bars; General aspects of joining several hollow-preforms to form hollow or tubular articles
    • B29C66/51Joining tubular articles, profiled elements or bars; Joining single elements to tubular articles, hollow articles or bars; Joining several hollow-preforms to form hollow or tubular articles
    • B29C66/52Joining tubular articles, bars or profiled elements
    • B29C66/522Joining tubular articles
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C66/00General aspects of processes or apparatus for joining preformed parts
    • B29C66/50General aspects of joining tubular articles; General aspects of joining long products, i.e. bars or profiled elements; General aspects of joining single elements to tubular articles, hollow articles or bars; General aspects of joining several hollow-preforms to form hollow or tubular articles
    • B29C66/51Joining tubular articles, profiled elements or bars; Joining single elements to tubular articles, hollow articles or bars; Joining several hollow-preforms to form hollow or tubular articles
    • B29C66/52Joining tubular articles, bars or profiled elements
    • B29C66/522Joining tubular articles
    • B29C66/5229Joining tubular articles involving the use of a socket
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/12Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives
    • C08J5/124Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives using adhesives based on a macromolecular component
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04Homopolymers or copolymers of esters
    • C09J133/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/062Copolymers with monomers not covered by C09J133/06
    • C09J133/066Copolymers with monomers not covered by C09J133/06 containing -OH groups
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • FMECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F16ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
    • F16LPIPES; JOINTS OR FITTINGS FOR PIPES; SUPPORTS FOR PIPES, CABLES OR PROTECTIVE TUBING; MEANS FOR THERMAL INSULATION IN GENERAL
    • F16L47/00Connecting arrangements or other fittings specially adapted to be made of plastics or to be used with pipes made of plastics
    • F16L47/02Welded joints; Adhesive joints
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C65/00Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor
    • B29C65/48Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding
    • B29C65/52Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding characterised by the way of applying the adhesive
    • B29C65/526Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding characterised by the way of applying the adhesive by printing or by transfer from the surfaces of elements carrying the adhesive, e.g. using brushes, pads, rollers, stencils or silk screens
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C66/00General aspects of processes or apparatus for joining preformed parts
    • B29C66/01General aspects dealing with the joint area or with the area to be joined
    • B29C66/05Particular design of joint configurations
    • B29C66/10Particular design of joint configurations particular design of the joint cross-sections
    • B29C66/11Joint cross-sections comprising a single joint-segment, i.e. one of the parts to be joined comprising a single joint-segment in the joint cross-section
    • B29C66/112Single lapped joints
    • B29C66/1122Single lap to lap joints, i.e. overlap joints
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C66/00General aspects of processes or apparatus for joining preformed parts
    • B29C66/70General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material
    • B29C66/71General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material characterised by the composition of the plastics material of the parts to be joined
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C66/00General aspects of processes or apparatus for joining preformed parts
    • B29C66/70General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material
    • B29C66/71General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material characterised by the composition of the plastics material of the parts to be joined
    • B29C66/712General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material characterised by the composition of the plastics material of the parts to be joined the composition of one of the parts to be joined being different from the composition of the other part
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C66/00General aspects of processes or apparatus for joining preformed parts
    • B29C66/70General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material
    • B29C66/73General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material characterised by the intensive physical properties of the material of the parts to be joined, by the optical properties of the material of the parts to be joined, by the extensive physical properties of the parts to be joined, by the state of the material of the parts to be joined or by the material of the parts to be joined being a thermoplastic or a thermoset
    • B29C66/739General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material characterised by the intensive physical properties of the material of the parts to be joined, by the optical properties of the material of the parts to be joined, by the extensive physical properties of the parts to be joined, by the state of the material of the parts to be joined or by the material of the parts to be joined being a thermoplastic or a thermoset characterised by the material of the parts to be joined being a thermoplastic or a thermoset
    • B29C66/7392General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material characterised by the intensive physical properties of the material of the parts to be joined, by the optical properties of the material of the parts to be joined, by the extensive physical properties of the parts to be joined, by the state of the material of the parts to be joined or by the material of the parts to be joined being a thermoplastic or a thermoset characterised by the material of the parts to be joined being a thermoplastic or a thermoset characterised by the material of at least one of the parts being a thermoplastic
    • B29C66/73921General aspects of processes or apparatus for joining preformed parts characterised by the composition, physical properties or the structure of the material of the parts to be joined; Joining with non-plastics material characterised by the intensive physical properties of the material of the parts to be joined, by the optical properties of the material of the parts to be joined, by the extensive physical properties of the parts to be joined, by the state of the material of the parts to be joined or by the material of the parts to be joined being a thermoplastic or a thermoset characterised by the material of the parts to be joined being a thermoplastic or a thermoset characterised by the material of at least one of the parts being a thermoplastic characterised by the materials of both parts being thermoplastics
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29KINDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2025/00Use of polymers of vinyl-aromatic compounds or derivatives thereof as moulding material
    • B29K2025/04Polymers of styrene
    • B29K2025/08Copolymers of styrene, e.g. AS or SAN, i.e. acrylonitrile styrene
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29KINDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2027/00Use of polyvinylhalogenides or derivatives thereof as moulding material
    • B29K2027/06PVC, i.e. polyvinylchloride
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29KINDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2055/00Use of specific polymers obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in a single one of main groups B29K2023/00 - B29K2049/00, e.g. having a vinyl group, as moulding material
    • B29K2055/02ABS polymers, i.e. acrylonitrile-butadiene-styrene polymers
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29KINDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2067/00Use of polyesters or derivatives thereof, as moulding material
    • B29K2067/003PET, i.e. poylethylene terephthalate
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29LINDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
    • B29L2023/00Tubular articles
    • B29L2023/22Tubes or pipes, i.e. rigid
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29LINDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
    • B29L2023/00Tubular articles
    • B29L2023/22Tubes or pipes, i.e. rigid
    • B29L2023/225Insulated
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04Acids; Metal salts or ammonium salts thereof
    • C08F220/06Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/12Esters of monohydric alcohols or phenols
    • C08F220/14Methyl esters, e.g. methyl (meth)acrylate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/20Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2433/00Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2433/04Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2433/06Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2433/00Presence of (meth)acrylic polymer

Definitions

  • the present invention relates to methods for cohesively (stoffschlüssigen) connecting plastic pipes as well as a pipe network of at least two plastic pipes.
  • bonding plastic pipes for example PVC pressure pipes
  • commonly used bonding agents comprise solid polymer that is dissolved in a suitable solvent or solvent system.
  • the adhesion principle is based on the swelling, dissolution and diffusion characteristics of the solvent.
  • the solvents diffuse into the base material, cause it to swell, and assisted by the dissolved incorporated polymer fraction, lead to the bonding of the components in the pressing operation.
  • the solvents are desorbed over an ill-defined period, such that a homogeneous bond is achieved.
  • This principle of pipe bonding technology is described e.g. in the European patent application EP 0 197 481 A2.
  • the concern of the present invention was to provide a pipe network that does not require the use of solvent-based bonding agents and in addition has an improved strength, in particular shear strength, of the adhesive bond.
  • a first subject matter of the invention is a method for cohesively connecting plastic pipes by means of a fitting
  • an adhesive is applied both onto the joining surface of the fitting as well as onto the joining surfaces of the pipe ends to be connected therewith.
  • fitting refers to the connecting pieces of a pipeline. These connection pieces enable e.g. the (particularly straight) connection of pipe sections, but also pipe connections for a change of direction or change of diameter as well as the connection to component parts.
  • the use of fittings enables the pipeline routing to be easily adapted to the external conditions, including e.g. circumventing obstacles, installing branches and changes of diameter etc. The route of a pipeline can thus be easily adapted to the constructional requirements.
  • fitting is commonly used everywhere in pipeline planning as well as in installation technology. In the context of the invention, plastic fittings are preferably employed.
  • a second subject matter of the present invention is a method for cohesively connecting plastic pipes
  • pipe connection is achieved by sliding a first pipe end together with a second pipe end, wherein the one pipe end represents a receiving pipe part and the other pipe end represents an insertion pipe part,
  • an adhesive is applied onto at least one (in particular on both) of the joining surfaces to be connected together, and after the pipe ends have been slid together, the adhesive is allowed to cure, characterized in that a (meth)acrylate adhesive is used as the adhesive.
  • the method according to the invention offers a series of advantages. Firstly, permanently stable, high strength pipe connections are enabled, which have a lifetime that corresponds to the lifetime of a pipe, and which meet the quality and verification requirements that apply in particular to pressure pipelines.
  • the bonded connection achieved by means of the method according to the invention has a very good light resistance, a very good solvent resistance, a very good resistance to hydrolysis, very good resistance to high and low temperatures and a very good impact resistance.
  • a very good shear strength of the bonded connection is achievable. In the context of the present invention, the shear strength can be tested in particular according to DIN EN ISO 9311-2.
  • connection technology is a particularly rapid strength build-up under usual curing conditions (e.g. at room temperature 20° C.), in particular in regard to the shear strength, thereby enabling plants to be started up more quickly.
  • the adhesive can be applied without problem, e.g. by static mixers.
  • the two methods according to the invention differ only in that in the first method the pipes are connected together with fittings, and in the second method the pipes are connected directly together.
  • the adhesive can be applied in all possible ways in the method according to the invention.
  • the adhesive is preferably applied with the aid of an application tool, in particular by brush coating. This enables a particularly uniform application in the desired adequate thickness.
  • the adhesive is allowed to cure particularly at ambient temperature that, depending on the climatic situation, is preferably about 10 to 35° C., for example 20° C. A very good strength of the bonded connection is achieved already after one hour.
  • the adhesive film thickness on the joining surface before assembly is in the range 0.1 mm to 3 mm, preferably 0.2 mm to 1.5 mm, particularly 0.2 mm to 0.6 mm.
  • These adhesive film thicknesses in connection with the employed (meth)acrylate adhesive afford pipe bonds with a quite particularly long service life.
  • diameter gaps of ⁇ 0.2 mm could also be joined.
  • the bonding connection between the joining surfaces is effected by sliding pipe and fitting or pipe and pipe together.
  • the method according to the invention is advantageously carried out in the context of a preferred embodiment, such that pipe and fitting or pipe and pipe are slid together without twisting.
  • outstandingly permanently secure pipe connections can also be produced in the context of the present invention if pipe and fitting or pipe and pipe are slid together with twisting, because a particular advantage of the present invention is that the inventively employed (meth)acrylate adhesives have a comparatively long open time (compared with solvent-based adhesives) and therefore also allow corrections or twisting when pipe and fitting or pipe and pipe are slid together, although even still better results are obtained when twisting is avoided.
  • the comparatively long open time enables the problem-free bonding of large diameter pipes, i.e. with diameters greater than 400 mm.
  • the method according to the invention is fundamentally suitable for securely bonding all types of plastic pipes.
  • the plastic pipes to be connected concern those based on thermoplastic polymers, in particular based on PVC (preferably PVC-U or PVC-C), ABS (acrylonitrile-butadiene-styrene copolymer), ASA (acrylic ester-styrene-acrylonitrile copolymer), ABS/ASA, and/or PET (polyethylene terephthalate).
  • the fittings are likewise preferably based on thermoplastic polymers, in particular based on those cited above.
  • PVC-C is the abbreviation according to DIN EN ISO 1043-1: 2002-06 for chlorinated polyvinyl chloride.
  • Chlorinated polyvinyl chloride can be manufactured by chlorinating polyvinyl chloride (PVC) in fluidized bed processes, dispersion processes or solution processes and is usually marketed as a colorless powder with a chlorine content of ca. 62-73% and a density of ca. 1.5-1.58 g/cm 3 .
  • the chlorination increases in particular the thermal stability and heat deformation resistance of the polyvinyl chloride.
  • PVC-U is the abbreviation according to DIN EN ISO 1043-1: 2002-06 for rigid PVC that can have plasticizer contents of 0-12 wt %.
  • Plastic pipes based on PVC-U to be bonded according to the invention are in particular free of plasticizer.
  • flexible PVC has plasticizer contents of >12 wt %.
  • a particular advantage of the present invention is that the joining parts to be connected may also consist of different plastic materials, and permanently secure pipe connections are enabled nevertheless.
  • another preferred embodiment of the present invention corresponds to when the joining parts consist of different plastic materials.
  • Another particular advantage of the present invention is that it enables a bonded connection that minimizes or even obviates the need for solvent.
  • the bonding principle of the usual bonding agents for pipe bonding is frequently based on, as illustrated in the introduction, the swelling, dissolution and diffusion behavior of the employed solvent.
  • the employed adhesive comprises less than 10 wt %, preferably less than 5 wt %, particularly less than 2 wt % or even no solvent.
  • a reduced solvent fraction serves not least the occupational health and safety.
  • reactive monomers are not solvents in the scope of the invention.
  • the inventively employed adhesive is a (meth)acrylate adhesive.
  • (meth)acrylate adhesives are adhesives that comprise acrylic acid and/or methacrylic acid and/or their esters. They particularly concern two-component adhesives.
  • Particularly preferred (meth)acrylate adhesives in the context of this invention are two-component reactive adhesives that comprise methacrylic acid esters, in particular methacrylic acid methyl ester (methyl methacrylate).
  • those (meth)acrylate adhesives are preferred, in which the reactive monomer system comprises at least 10 wt % methyl methacrylate, preferably at least 20 wt % methyl methacrylate, in particular at least 30 wt % methyl methacrylate, each wt % relative to the total reactive monomer system.
  • the reactive monomer system comprises at least 40 wt % methyl methacrylate, preferably at least 50 wt % methyl methacrylate, in particular at least 60 wt % methyl methacrylate, each wt % relative to the total reactive monomer system.
  • the monomers employed in the (meth)acrylate adhesive such as in particular the methyl methacrylate, can be polymerized by a radical chain reaction.
  • a reactive radical is needed, which is mainly afforded by a peroxide when an accelerator is added to it.
  • Suitable peroxides such as e.g. dibenzoyl peroxide
  • suitable accelerators such as e.g. tertiary aromatic amines, such as in particular dimethyl-p-toluidine, are known per se.
  • the (meth)acrylate system can be processed in that e.g. a first component A comprises at least one polymerizable monomer component based on (meth)acrylate, and a curing agent, and a second component B comprises at least one polymerizable monomer component based on (meth)acrylate, and a catalytic component for catalyzing the curing reaction (the so-called accelerator).
  • the components A and B can be mixed in the required proportions prior to application onto the joining parts and then dosed onto the joining parts.
  • the mixing is particularly effected in a static mixer. Still, it is also possible to apply the components directly onto the joining parts and to realize the necessary mixing through the contact pressure on the joining parts; this is particularly advantageous in regard to the method according to the invention, because it is labor-saving.
  • the at least one polymerizable monomer component based on (meth)acrylate can comprise any monomer component that is suitable for use in the (meth)acrylate adhesives, in particular comprising acrylic acid and/or methacrylic acid and/or their esters.
  • Methyl methacrylate is preferably comprised.
  • Polymerizable monomer components based on (meth)acrylate are preferably comprised in a total amount of 30-80 wt %, relative to the total adhesive composition.
  • the monomer system preferably comprises methyl methacrylate.
  • the methyl methacrylate is preferably comprised in amounts of 20-70 wt %, particularly 30-60 wt %, relative to the total adhesive composition.
  • esters of methacrylic acid or acrylic acid can preferably be additionally employed, e.g. hydroxyethyl methacrylate and/or hydroxypropyl methacrylate, preferably in a total amount of 5-50 wt %, particularly 10-30 wt %, relative to the total adhesive composition.
  • acidic monomers can be additionally employed, in particular methacrylic acid, preferably in a total amount of 0.5-10 wt %, particularly 1-5 wt %, relative to the total adhesive composition.
  • methacrylic acid preferably in a total amount of 0.5-10 wt %, particularly 1-5 wt %, relative to the total adhesive composition.
  • the addition of the acidic monomer, in particular methacrylic acid, combined with the other ingredients of the adhesive particularly improves the heat deformation resistance of the pipe bond, but also the curing behaviour and also the adhesion properties to the pipe materials as well as the tensile strength.
  • methacrylic acid is therefore associated with great advantages for the invention and therefore corresponds to a particularly preferred embodiment of the invention.
  • a particularly preferred example of a methacrylate with polar groups is the hydroxyethyl methacrylate monomer that is available e.g. as Mhoromer BM 905 from Evonik.
  • the total composition comprises
  • di or higher functional monomers can be additionally employed as the polymerizable monomer components, such as e.g. ethylene glycol dimethacrylate, propylene glycol dimethacrylate and/or 1,1,1-trimethylolpropane trimethacrylate. This improves in particular the heat deformation resistance of the pipe bonding.
  • the total amount of such di or higher functional monomers can be e.g. 0 to 20 wt %, preferably 0.1 to 10 wt %, in particular 0.1 to 5 wt %, relative to the total composition.
  • Peroxides, hydroperoxides, peroxy esters, peroxy salts, peroxy acids and/or mixtures thereof come into consideration as the peroxide-based curing agents.
  • Hydroperoxides such as e.g. cumene hydroperoxide or diisopropylbenzene hydroperoxide are particularly preferred. Cumene hydroperoxide is most preferred.
  • tert-Butyl hydroperoxide (TBH), tert-butyl perbenzoate (TBPB) and benzoyl peroxide (BPO) are also suitable. Typically, they are suitably employed in a total quantity of about 0.5 wt % to 3 wt % of the total composition.
  • stabilizers such as e.g. products based on sterically hindered phenols, hydroquinones or quinones, prevents an unwanted premature initiation of radical chain reactions and increases the storage stability of the composition.
  • Preferred stabilizers that can be comprised in both components are selected, independently of one another, from thiazines, hydroquinones, quinones, sterically hindered phenols (e.g. 2,6-di-tert-butyl-4-methylphenol), organic acids and compounds that possess an oxazole functionality.
  • thiazines hydroquinones
  • quinones quinones
  • sterically hindered phenols e.g. 2,6-di-tert-butyl-4-methylphenol
  • organic acids and compounds that possess an oxazole functionality e.g. 2,6-di-tert-butyl-4-methylphenol
  • the total amount of the stabilizers can be in the range of e.g. 0.1 to 10 wt %, relative to the total composition.
  • Substances that can catalyze the decomposition of the curing agent, in particular the peroxide to radicals, can be employed as the catalytic components for catalyzing the curing reaction.
  • Tertiary amines such as e.g. N,N-dimethyl-p-toluidine, N,N-dihydroxyethyl-p-toluidine, dimethylaniline, diethylaniline, N,N-diethyl-p-toluidine and combinations thereof are suitable.
  • Imines are also suitable, such as e.g. the imine from butanal and aniline.
  • Dihydropyridine derivatives such as e.g. 3,5-diethyl-1,2-dihydro-1-phenyl-2-propylpyridine, are likewise suitable.
  • Transition metal salts for example copper and/or cobalt salts, such as copper octanoate, which are preferably soluble in organic media, can likewise be employed. It is particularly preferred to employ a transition metal salt in combination with a tertiary amine, an imine or dihydropyridine derivative as the catalytic components to catalyze the curing reaction.
  • the suitable total amount of the catalytic component(s) for catalyzing the curing reaction is preferably in the range 0.01 to 5 wt %, relative to the total composition.
  • Components for improving the impact resistance are in particular elastomers, preferably chlorosulfonated polyethylene (so-called “Hypalon®” from DuPont).
  • Chlorosulfonated polyethylene can be comprised e.g. preferably in amounts of 5-50 wt %, in particular 10-30 wt %, in the total composition.
  • Chlorosulfonated polyethylene can be manufactured e.g. by the simultaneous treatment of polyethylene with chlorine and sulfur dioxide.
  • Commercially available chlorosulfonated polyethylene types comprise ca. 25-45% chlorine and 0.8-1.5% sulfur.
  • Preferred employable components for improving the impact resistance are in particular also styrene-acrylonitrile-butadiene copolymers (such as e.g. Blendex 338 from Chemtura), abbreviated to ABS copolymers.
  • ABS copolymers belong to the group of the elastomer-modified thermoplastics.
  • the inventively employable ABS copolymers preferably concern thermoplastic and elastomeric polymer blends, whose discontinuous, elastomeric phase of homopolymers or copolymers of buta-1,3-diene is dispersed in a continuous phase of rigid, thermoplastic styrene-acrylonitrile copolymers.
  • Styrene-acrylonitrile-butadiene copolymers can be comprised for example in amounts of preferably 5-50 wt %, in particular 10-30 wt %, in the total composition.
  • any suitable component can be employed in the present invention to improve the impact resistance.
  • the component to improve the impact resistance of the present invention can be selected from a plurality of elastomeric materials.
  • Polyacrylate, styrene/butadiene/styrene (SBS) copolymer, styrene/isoprene/styrene (SIS) copolymer or styrene/butadiene copolymer can be employed for example.
  • elastomers are selected from the group consisting of acrylate-butadiene copolymer, butadiene, chloroprene, ethylene-propylene, ethylene-propylene-diene, isoprene, isobutylene, isobutylene-isoprene (butyl rubber), styrene-butadiene, styrene-isoprene, acrylonitrile-butadiene, acrylonitrile-chloroprene, vinyl pyridine-butadiene, vinyl pyridine-styrene-butadiene, chloroisobutylene-isoprene (chlorobutyl rubber), bromoisobutylene-isoprene (bromobutyl rubber), dialkysiloxane, polypropylene oxide, polyester urethane polyether urethane as well as their mixtures.
  • reactive liquid polymers can be employed.
  • Reactive liquid polymers comprise functional groups, generally on their terminal ends, and react in situ with the resin to form elastomeric domains.
  • Exemplary reactive liquid polymers are carboxy-terminated butadiene nitrile (CTBN), amine-terminated butadiene nitrile (ATBN), hydroxy-terminated butadiene nitrile (HTBN), epoxy-terminated butadiene nitrile (ETBN), mercapto-terminated butadiene nitrile (MTPN) and phenoxy-terminated butadiene nitrile (PTBN).
  • Particularly useful components for improving the impact resistance are certainly chlorosulfonated polyethylene, styrene-acrylonitrile-butadiene copolymers (such as e.g. Blendex 338 from Chemtura) and/or nitrile rubber.
  • chlorosulfonated polyethylenes such as for example Hypalon 20 or Hypalon 30 from DuPont, as well as styrene-acrylonitrile-butadiene copolymers (such as e.g. Blendex 338 from Chemtura), wherein it is preferred to employ a combination of chlorosulfonated polyethylenes and styrene-acrylonitrile-butadiene copolymers. In this way, particularly good strength values could be obtained for the pipe connection.
  • the employable total amount of the component(s) for improving the impact resistance can preferably be in the range 5-70 wt %, in particular 10-60 wt %, relative to the total composition.
  • a first component comprising:
  • the polymerizable monomers of the first component are preferably present in amounts of 20 to 60 wt %, in particular 30 to 50 wt % of the total weight of the first component.
  • the curing agent, in particular based on peroxide, of the first component is preferably present in amounts of 0.1 to 5 wt %, in particular 0.2 to 4 wt % of the total weight of the first component.
  • the stabilizer of the first component is preferably present in amounts of 0.1 to 5 wt %, in particular 0.2 to 4 wt % of the total weight of the first component.
  • the polymerizable monomers of the second component are preferably present in amounts of 10 to 90 wt %, in particular 30 to 80 wt % of the total weight of the second component.
  • the catalytic component of the second component is preferably present in amounts of 0.01 to 5 wt %, in particular 0.02 to 4 wt % of the total weight of the second component.
  • the stabilizer of the second component is preferably present in amounts of 0.01 to 5 wt %, in particular 0.02 to 4 wt % of the total weight of the second component.
  • a curable (meth)acrylate adhesive that is preferably employable in the context of the invention comprises: a first component, comprising:
  • a first component comprising:
  • Fumed silica is particularly suitable as the thickener.
  • inventively employable (meth)acrylate adhesives can comprise, as needed, additional optional components, for example an optional dye component.
  • Chelating agents can likewise be employed in the (meth)acrylate adhesives, in particular for the control and prevention of premature peroxide decomposition and polymerization, as well as to remove traces of metallic impurities.
  • a particularly preferred chelating agent is the tetrasodium salt of ethylenediaminetetraacetic acid (EDTA).
  • EDTA ethylenediaminetetraacetic acid
  • Useful total amounts of chelating agent, in particular EDTA are typically in the range of 0.01 wt % to 5 wt % of the total composition.
  • the chelating agent, in particular EDTA can be comprised in a total amount of 0.02 wt % to 3 wt % of the total composition.
  • Organic acids can be used in the present invention.
  • exemplary suitable organic acids are carboxylic acids.
  • Suitable carboxylic acids are for example maleic acid as well as fumaric acid.
  • the useful total amount of the optional organic acid is generally in the range of preferably 0 wt % to 9 wt %, relative to the total composition.
  • the organic acid can be comprised in a total amount of 0.1 wt % to 5 wt %, relative to the total composition.
  • a preferable employable curable two-component (meth)acrylate adhesive in the context of the invention comprises in the total composition
  • the hydroxyethyl methacrylate and/or hydroxypropyl methacrylate is preferably comprised in the component (a) namely in a total amount of 5-15 wt %, relative to the component in question.
  • the composition according to the invention may optionally comprise a so-called open time extender, in particular based on wax, preferably in both components of the total composition.
  • Open time extenders serve to extend the open time and are known per se to the person skilled in the art.
  • Each suitable open time extender can be optionally comprised in the compositions according to the invention.
  • Suitable open time extenders include a series of various waxes, wherein paraffin wax such as for example “IGI 1977” from the International Group is preferred.
  • Useful amounts of the optional open time extender are typically in the range of 0.1 wt % to 3 wt %, preferably 0.2 wt % to 1.5 wt %, relative to the total composition.
  • the inventively used plastic pipes concern pressure pipes.
  • Pressure pipes are known per se to the person skilled in the art and are employed in pressure pipelines.
  • a pipeline in which a higher pressure than atmospheric pressure prevails, is called a pressure pipeline.
  • Pressure-less applications i.e. gravity lines or open-channel lines, can of course, likewise be inventively realized.
  • pipe connections that can be inventively provided are particularly employable for transporting water, however, other media can of course also be transported, such as e.g. glycol mixtures that are used for example as coolants. However, the transport of water is particularly preferred.
  • the pipe connections according to the invention are consequently particularly employed for potable water lines, industrial water lines, and/or for pressure drainage.
  • the methods according to the invention for cohesively connecting plastic pipes afford pipe networks of at least two plastic pipes.
  • a further subject matter of the present invention is consequently a pipe network made up of at least two plastic pipes with or without a fitting insert between the pipe ends, suitable in particular for potable water lines, industrial water lines, and/or for pressure drainage, characterized in that the joined surfaces of the joined parts connected to one another are attached with a two-component (meth)acrylate adhesive.
  • the shear strength of bonded PVC-U pipe connections was tested according to DIN EN ISO 9311-2. According to DIN EN 14814 the minimum requirement for the shear strength of the pipe connection at a test temperature of 23° C., 1 h after bonding is 0.4 MPa, 24 h after bonding 1.5 MPa and 480 h after bonding 7.0 MPa.
  • a 75 mm long pipe section (material: PVC-U; 40 mm external diameter) was firstly bonded with an inventive 2-component (meth)acrylate adhesive to a fitting made of the same material over a length of 20 mm, and the shear strength of the connection was subsequently tested according to DIN EN ISO 9311-2.
  • the inventively employed 2-component (meth)acrylate adhesive had the following frame formulation:
  • the shear strength of the connection determined according to DIN EN 14814 at a test temperature of 23° C., 1 h after bonding was 5.0 MPa, 24 h after bonding 16 MPa and 480 h after bonding 20.0 MPa.
  • the final strength value can be taken as the 480 h value. Consequently, the invention already after 24 h enables a strength that is more than double that required by DIN EN 14814.
  • the connection already after lh the connection exhibits a very high strength that is a multiple of the 24 h requirement of DIN EN 14814.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Lining Or Joining Of Plastics Or The Like (AREA)
US14/299,325 2011-12-09 2014-06-09 Process for the adhesive bonding of plastics pipes by means of (meth)acrylate adhesive Active 2034-09-23 US9868250B2 (en)

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DE102011088123 2011-12-09
DE102011088123A DE102011088123A1 (de) 2011-12-09 2011-12-09 Verfahren zum stoffschlüssigen Verbinden von Kunststoff-Rohren
DE102011088123.9 2011-12-09
PCT/EP2012/073291 WO2013083406A1 (de) 2011-12-09 2012-11-22 Verfahren zum stoffschlüssigen verbinden von kunststoff-rohren mit (meth) acrylat-klebstoff

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10400140B2 (en) 2013-06-17 2019-09-03 Tesa Se Reactive 2-component adhesive film system
US11898067B2 (en) 2016-12-05 2024-02-13 Tesa Se Reactive 2-component adhesive system in film form having improved heat-and-humidity resistance

Citations (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3276929A (en) 1960-08-20 1966-10-04 Degussa Method of forming a sleeved joint over shaped polyolefin bodies
JPS54141826A (en) 1978-04-24 1979-11-05 Lord Corp Composition for bonding structure
US4200480A (en) 1976-07-14 1980-04-29 Pratt & Lambert, Inc. Adhesive joining of pipes
JPS6072971A (ja) 1983-09-30 1985-04-25 Mitsui Constr Co Ltd パイプ用接着剤
JPS6195928A (ja) 1984-10-18 1986-05-14 Kyushu Sekisui Kogyo Kk Frp管とfrp継手との接続方法
EP0197481A2 (de) 1985-04-06 1986-10-15 Henkel Kommanditgesellschaft auf Aktien Mittel zum Verkleben von Formteilen aus Hart-PVC
US5003016A (en) 1989-01-17 1991-03-26 Minnesota Mining And Manufacturing Company Surface activator for redox-initiated adhesives
JPH0886388A (ja) 1994-09-16 1996-04-02 Sanyo Electric Co Ltd 冷凍回路の配管接続装置
US5656345A (en) 1995-06-07 1997-08-12 Illinois Tool Works, Inc. Adhesive compositions and adhesively joined pipe segments
JP2001343094A (ja) 2000-06-01 2001-12-14 Mitsubishi Plastics Ind Ltd 管の接続方法
JP2003207087A (ja) 2002-01-09 2003-07-25 Sekisui Chem Co Ltd 複層管の接合構造および接合方法
JP2003294174A (ja) 2001-05-22 2003-10-15 Nippon Steel Corp 樹脂ライニング鋼管およびその製造方法
CN1835993A (zh) 2003-08-13 2006-09-20 陶氏环球技术公司 将管道系统和管道连接到装备、固定物、设备、结构和器具的方法
CN101165133A (zh) 2006-10-17 2008-04-23 湖北回天胶业股份有限公司 双组分丙烯酸酯结构胶粘剂及其制备方法
CN101238186A (zh) 2005-08-11 2008-08-06 3M创新有限公司 作为金属基底涂层的互穿聚合物网络及其制造方法
WO2009108751A1 (en) 2008-02-28 2009-09-03 Lubrizol Advanced Materials, Inc. Adhesively secured, fluid-tight pipe joint of pvc/cpvc pipe and fitting
US7816453B2 (en) 2001-07-10 2010-10-19 Ips Corporation Adhesive compositions for bonding and filling large assemblies
WO2011002876A2 (en) 2009-06-30 2011-01-06 Henkel Corporation Ultrafast heat/room temperature adhesive composition for bonding applications
JP2011514501A (ja) 2008-02-14 2011-05-06 ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェン 熱交換器の製造方法
JP2011515528A (ja) 2008-03-21 2011-05-19 ジャクレ 構造用接着剤組成物
JP6195928B2 (ja) 2012-07-18 2017-09-13 マーレ インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツングMAHLE International GmbH 内燃機関用のピストン

Patent Citations (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3276929A (en) 1960-08-20 1966-10-04 Degussa Method of forming a sleeved joint over shaped polyolefin bodies
US4200480A (en) 1976-07-14 1980-04-29 Pratt & Lambert, Inc. Adhesive joining of pipes
JPS54141826A (en) 1978-04-24 1979-11-05 Lord Corp Composition for bonding structure
JPS6072971A (ja) 1983-09-30 1985-04-25 Mitsui Constr Co Ltd パイプ用接着剤
JPS6195928A (ja) 1984-10-18 1986-05-14 Kyushu Sekisui Kogyo Kk Frp管とfrp継手との接続方法
EP0197481A2 (de) 1985-04-06 1986-10-15 Henkel Kommanditgesellschaft auf Aktien Mittel zum Verkleben von Formteilen aus Hart-PVC
US5003016A (en) 1989-01-17 1991-03-26 Minnesota Mining And Manufacturing Company Surface activator for redox-initiated adhesives
JPH0886388A (ja) 1994-09-16 1996-04-02 Sanyo Electric Co Ltd 冷凍回路の配管接続装置
US5656345A (en) 1995-06-07 1997-08-12 Illinois Tool Works, Inc. Adhesive compositions and adhesively joined pipe segments
JP2001343094A (ja) 2000-06-01 2001-12-14 Mitsubishi Plastics Ind Ltd 管の接続方法
JP2003294174A (ja) 2001-05-22 2003-10-15 Nippon Steel Corp 樹脂ライニング鋼管およびその製造方法
US7816453B2 (en) 2001-07-10 2010-10-19 Ips Corporation Adhesive compositions for bonding and filling large assemblies
JP2003207087A (ja) 2002-01-09 2003-07-25 Sekisui Chem Co Ltd 複層管の接合構造および接合方法
CN1835993A (zh) 2003-08-13 2006-09-20 陶氏环球技术公司 将管道系统和管道连接到装备、固定物、设备、结构和器具的方法
CN101238186A (zh) 2005-08-11 2008-08-06 3M创新有限公司 作为金属基底涂层的互穿聚合物网络及其制造方法
CN101165133A (zh) 2006-10-17 2008-04-23 湖北回天胶业股份有限公司 双组分丙烯酸酯结构胶粘剂及其制备方法
JP2011514501A (ja) 2008-02-14 2011-05-06 ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェン 熱交換器の製造方法
WO2009108751A1 (en) 2008-02-28 2009-09-03 Lubrizol Advanced Materials, Inc. Adhesively secured, fluid-tight pipe joint of pvc/cpvc pipe and fitting
JP2011515528A (ja) 2008-03-21 2011-05-19 ジャクレ 構造用接着剤組成物
WO2011002876A2 (en) 2009-06-30 2011-01-06 Henkel Corporation Ultrafast heat/room temperature adhesive composition for bonding applications
JP6195928B2 (ja) 2012-07-18 2017-09-13 マーレ インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツングMAHLE International GmbH 内燃機関用のピストン

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DIN EN ISO 1043-1.
DIN EN ISO 14814.
DIN EN ISO 9311-2.
International Search Report for PCT/EP2012/073291, 2 pages.

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10400140B2 (en) 2013-06-17 2019-09-03 Tesa Se Reactive 2-component adhesive film system
US10711163B2 (en) 2013-06-17 2020-07-14 Tesa Se Reactive 2-component adhesive film system
US11898067B2 (en) 2016-12-05 2024-02-13 Tesa Se Reactive 2-component adhesive system in film form having improved heat-and-humidity resistance

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MX2014006765A (es) 2014-08-01
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CN103974816A (zh) 2014-08-06
MX337562B (es) 2016-03-10
EP2788168B1 (de) 2019-01-02
JP5977362B2 (ja) 2016-08-24
JP2015504928A (ja) 2015-02-16
WO2013083406A1 (de) 2013-06-13
US20140284924A1 (en) 2014-09-25
AU2012348675A1 (en) 2014-07-03

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